ChemInform Abstract: The Tunable Transmission of the Aromatic Character of the Aglycone Through the Anomeric Effect in C-Nucleosides Drives Its Own Sugar Conformation: A Thermodynamic Study.

I. LUYTEN; C. THIBAUDEAU; A. SANDSTROEM; J. CHATTOPADHYAYA

doi:10.1002/chin.199738271

ChemInform Abstract: The Tunable Transmission of the Aromatic Character of the Aglycone Through the Anomeric Effect in C-Nucleosides Drives Its Own Sugar Conformation: A Thermodynamic Study.

ChemInform ◽

10.1002/chin.199738271 ◽

2010 ◽

Vol 28 (38) ◽

pp. no-no

Author(s):

I. LUYTEN ◽

C. THIBAUDEAU ◽

A. SANDSTROEM ◽

J. CHATTOPADHYAYA

Keyword(s):

Thermodynamic Study ◽

Anomeric Effect ◽

Aromatic Character ◽

Sugar Conformation

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The tunable transmission of the aromatic character of the aglycone through the anomeric effect in C-nucleosides drives its own sugar conformation: A thermodynamic study

Tetrahedron ◽

10.1016/s0040-4020(97)00302-5 ◽

1997 ◽

Vol 53 (18) ◽

pp. 6433-6464 ◽

Cited By ~ 12

Author(s):

Ingrid Luyten ◽

Christophe Thibaudeau ◽

Anders Sandström ◽

Jyoti Chattopadhyaya

Keyword(s):

Thermodynamic Study ◽

Anomeric Effect ◽

Aromatic Character ◽

Sugar Conformation

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THERMODYNAMIC STUDY OF MICRO SCALE ORGANIC RANKINE CYCLE (ORC) USING MODIFIED GOUY-STODOLA EQUATION

Proceeding of First Thermal and Fluids Engineering Summer Conference ◽

10.1615/tfesc1.ecv.012774 ◽

2016 ◽

Author(s):

Bhavesh Patel ◽

Vaibhav Jain ◽

Surendra Singh kachhwaha ◽

Nanji J. Hadia

Keyword(s):

Organic Rankine Cycle ◽

Rankine Cycle ◽

Thermodynamic Study ◽

Micro Scale

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Reactions of an Aluminium(I) Reagent with 1,2-, 1,3- and 1,5-Dienes: Dearomatisation, Reversibility, and a Pericyclic Mechanism

10.26434/chemrxiv.11400171.v1 ◽

2019 ◽

Author(s):

Clare Bakewell ◽

Martí Garçon ◽

Richard Y Kong ◽

Louisa O'Hare ◽

Andrew J. P. White ◽

...

Keyword(s):

Reaction Mechanism ◽

Dft Calculations ◽

Transition State ◽

Reaction Pathways ◽

Aromatic Rings ◽

Aromatic Character ◽

Pericyclic Reaction

The reactions of an aluminium(I) reagent with a series of 1,2-, 1,3- and 1,5-dienes are reported. In the case of 1,3-dienes the reaction occurs by a pericyclic reaction mechanism, specifically a cheletropic cycloaddition, to form aluminocyclopentene containing products. This mechanism has been interrogated by stereochemical experiments and DFT calculations. The stereochemical experiments show that the (4+1) cycloaddition follows a suprafacial topology, while calculations support a concerted albeit asynchronous pathway in which the transition state demonstrates aromatic character. Remarkably, the substrate scope of the (4+1) cycloaddition includes dienes that are either in part, or entirely, contained within aromatic rings. In these cases, reactions occur with dearomatisation of the substrate and can be reversible. In the case of 1,2- or 1,5-dienes complementary reactivity is observed; the orthogonal nature of the C=C π-bonds (1,2-diene) and the homoconjugated system (1,5-diene) both disfavour a (4+1) cycloaddition. Rather, reaction pathways are determined by an initial (2+1) cycloaddition to form an aluminocyclopropane intermediate which can in turn undergo insertion of a further C=C π-bond leading to complex organometallic products that incorporate fused hydrocarbon rings.

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